6,7-dimethoxy-4-methyl-3,4-dihydro-1H-naphthalen-2-one | 1315171-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6,7-dimethoxy-4-methyl-3,4-dihydro-1H-naphthalen-2-one
• CAS: 1315171-95-9
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: NHRZZQJPACNMBB-UHFFFAOYSA-N

物化性质

• 沸点：
  344.3±42.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-4-methyl-3,4-dihydro-1H-naphthalen-2-one 在 盐酸 、 三乙胺 、 diborane(6) 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 6-benzyl-10,11-dimethoxy-8β-methyl-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridine hydrochloride
  参考文献：
  名称：

  Probing the Steric Space at the Floor of the D₁ Dopamine Receptor Orthosteric Binding Domain: 7α-, 7β-, 8α-, and 8β-Methyl Substituted Dihydrexidine Analogues

  摘要：

  To probe the space at the floor of the orthosteric ligand binding site in the dopamine D-1 receptor, four methylated analogues of dihydrexidine (DHX) were synthesized with substitutions at the 7 and 8 positions. The 8 alpha-axial, 8 beta-equatorial, and 7 alpha-equatorial were synthesized by photochemical cyclization of appropriately substituted N-benzoyl enamines, and the 7 beta-axial analogue was prepared by an intramolecular Henry reaction. All of the methylated analogues displayed losses in affinity when compared to DHX (20 nM): 8 beta-Me-ax-DHX (270 nM), 8 alpha-Me-eq-DHX (920 nM), 7 beta-Me-eq-DHX (6540 nM), and 7 alpha-Me-ax-DFLX (>10000 nM). Molecular modeling studies suggest that although the disruption of an aromatic interaction between Phe203(54.7) and Phe288(6.51) is the cause for the 14-fold loss in affinity associated with 8 beta-axial substitution, unfavorable steric interactions with Ser107(3.36) result in the more dramatic decreases in binding affinity suffered by the rest of the analogues.

  DOI：

  10.1021/jm200334c
• 作为产物：
  描述：

  2-iodo-4,5-dimethoxyphenylacetic acid methyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium tert-butylate 、 氢气 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 乙腈 为溶剂， 20.0~125.0 ℃ 、413.7 kPa 条件下， 反应 96.75h， 生成 6,7-dimethoxy-4-methyl-3,4-dihydro-1H-naphthalen-2-one
  参考文献：
  名称：

  Probing the Steric Space at the Floor of the D₁ Dopamine Receptor Orthosteric Binding Domain: 7α-, 7β-, 8α-, and 8β-Methyl Substituted Dihydrexidine Analogues

  摘要：

  To probe the space at the floor of the orthosteric ligand binding site in the dopamine D-1 receptor, four methylated analogues of dihydrexidine (DHX) were synthesized with substitutions at the 7 and 8 positions. The 8 alpha-axial, 8 beta-equatorial, and 7 alpha-equatorial were synthesized by photochemical cyclization of appropriately substituted N-benzoyl enamines, and the 7 beta-axial analogue was prepared by an intramolecular Henry reaction. All of the methylated analogues displayed losses in affinity when compared to DHX (20 nM): 8 beta-Me-ax-DHX (270 nM), 8 alpha-Me-eq-DHX (920 nM), 7 beta-Me-eq-DHX (6540 nM), and 7 alpha-Me-ax-DFLX (>10000 nM). Molecular modeling studies suggest that although the disruption of an aromatic interaction between Phe203(54.7) and Phe288(6.51) is the cause for the 14-fold loss in affinity associated with 8 beta-axial substitution, unfavorable steric interactions with Ser107(3.36) result in the more dramatic decreases in binding affinity suffered by the rest of the analogues.

  DOI：

  10.1021/jm200334c